Ammonium formate → HCID 68291802, compound

HRID 72900Notes

Reaction equation

HRID 72900 reaction equation
C([N:8]1[CH2:25][C:12]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[O:11][CH:10]([CH:26]=[CH2:27])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[CH2:26]([CH:10]1[O:11][C:12]2([CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:16][CH2:17]2)[CH2:25][NH:8][CH2:9]1)[CH3:27]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68291372Tert-butyl 10-benzyl-8-vinyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 68291802HCID 68291802, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of tert-butyl 10-benzyl-8-vinyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate (3.10 g, 8.32 mmol) in methanol (60 mL) was added Pd(OH)2 (1.40 g, 9.99 mmol) and ammonium formate (10.5 g, 166 mmol) and the mixture heated at 55° C. for 20 min. The reaction mixture was filtered, concentrated to −10 mL, then diluted with dichloromethane and saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer extracted with dichloromethane (5×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide tert-butyl 4-ethyl-5-oxa-2,9-diazaspiro[5.5]undecane-9-carboxylate (2.27 g, 7.99 mmol, 96%). ESI-MS m/z calc. 284.21. Found 285.1 (M+1)+; Retention time: 1.09 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated to −10 mL
  3. additiondiluted with dichloromethane and saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with dichloromethane (5×20 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-243e76c409b541459761d6390dbefebf
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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